Carbamate → (Quinolin-3-yl)methanol

HRID 539506

반응식

HRID 539506 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11](=O)([O-:13])N.[BH4-].[Na+]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:13])[CH:2]=1

참가 물질

5

반응물 3

HCID 276Carbamate2회HCID 7047Quinoline2회HCID 4311764Sodium borohydride

생성물 1

HCID 12662983(Quinolin-3-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Synthesis of compounds ERW1041A, B, C, D, E, and 1069 were synthesized using the methods of Choi et al. Chemistry & Biology, Volume 12, Issue 4, Pages 469-475, except the amino-acid amines are protected by a quinoline-containing carbamate. This quinoline-containing carbamate is synthesized by reducing 3-quinolylcarbaldehyde with sodium borohydride in THF followed by an aqueous workup and flash chromatography yielding 3-quinolylcarbinol. para-Nitro-phenylchloroformate is reacted with 3-quinolylcarbinol in methylene chloride and N-methyl morpholine to give a carbonate of 3-quinoline methanol and para-Nitro-phenol. After purification by flash chromatography, this carbonate is reacted with the methyl ester of the amino acid in neat DMF to give the named compounds.

후처리

  1. customSynthesis of compounds ERW1041A, B, C, D, E, and 1069
  2. customwere synthesized
  3. customis synthesized

출처 및 근거

ORD 기록
ord-081ecec58c714981b4aae8a58db36932
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871718B2

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